Some regions (like my own in New England) are over saturating, others at 90% occupancy sound pretty far from it.

I completely disagree with the advice given repeatedly above that you should have any sort of dialogue or explanation for a rent increase.

Pick a house that is completely renovated.

Why would I invest in deals with a 4-6% ROI that will cash flow a couple hundred a month (if I’m lucky) and go through the trouble/risk of property ownership when I can get similar returns from other completely passive investments with practically 0 risk?

I know this sounds unreal, but I swear, every word is solid gold true. 

I'd be interested in a Chicago Discord group sounds like cool software and a way to connect.

It's not possible to answer the question without defining the scope of what you want...a swim spa style system craned in over the roof could be a couple weeks if it's in stock and can be delivered ASAP...then you just complete decking and landscape and it's finished.

Sounds exaggerated?

Completely burnt out.

Both sides have been rented out and the last second repairs are finally getting complete.